Sebum is skin oil which is produced by sebocytes (cells of the sebaceous glands in the skin) and is then secreted to the skin surface. A frequent and undesirable skin condition is “oily skin,” the condition which results from the excessive amount of sebum on the skin. Oily skin is associated with a shiny, undesirable appearance and a disagreeable tactile sensation and affects various age groups. Carboxyalkylates of branched alcohols are compounds which provide skin benefits such as sebum suppression.
For example, Harichian et al., U.S. Pat. No. 6,534,073 discloses cosmetic methods and compositions for conditioning human skin by topical application to the skin of cosmetic compositions containing carboxymethylates of branched alcohols. While a process for making carboxymethylates of branched alcohols, and/or ethoxylates thereof is disclosed, a need still exists for even more effective and efficient commercial scale processes, allowing use of smaller amounts and/or less expensive and/or less toxic starting materials, and resulting in overall cost efficiency.
Springman, U.S. Pat. No. 3,992,443 (hereinafter “Springmann '443”) discloses a process for the carboxymethylation of alcohols or ether alcohols in a single stage. Springmann '443 teaches the use of both straight chain and branched alcohols as suitable starting alcohols. However, it is believed the carboxymethylation reaction can be run at conditions to further maximize efficiency, ease of industrial scale production, and cost effectiveness.
Harichian et al., Pub. No. U.S. 2004/0018948 and U.S. 2004/0013631 disclose a process of synthesizing a carboxyethylate or higher carboxyalkylate comprising:
(a) combining a branched alcohol with a compound selected from the group consisting of chloroacetic acid, chloropropionic acid, chlorobutyric acid, and mixtures thereof to form a heterogeneous reaction mixture; (b)stirring and heating said heterogeneous reaction mixture at slight reflux under nitrogen;(c) cooling to room temperature; (d) filtering and washing to form a paste; (e) dissolving said paste in water; (f) acidifying with HCl; (g) extracting said acidified paste with chloroform or hexane; (h) removal of chloroform to form the carboxyalkylate compounds.
A need remains for improved processes for making carboxy-alkylates, particularly carboxymethylates, of branched alcohols.